Bertie Wooster and Orlo Porter

Orlo Porter was at school with Bertie Wooster chapters 2, 6
Orlo Porter sells insurance to Bertie Wooster chapters 2, 9
Orlo Porter is jealous of Bertie Wooster chapters 2, 14
Bertie Wooster deceives Orlo Porter chapters 2, 17
Orlo Porter threatens Bertie Wooster chapters 6, 7, 14, 16, 17
Bertie Wooster fears Orlo Porter chapters 7, 14
Orlo Porter loathes Bertie Wooster chapters 7, 8
Orlo Porter suspects Bertie Wooster chapters 8, 15

They deal with each other in Aunts Aren't Gentlemen 2, 6, 7, 8, 9, 14, 15, 16, 17, 18.

Scenes they share

Driving to see Murgatroyd, Bertie gets stuck behind the protest march and sits watching it.Chapters 1–2
Driving home drowsy from lunch, Bertie naps in a wood and is woken by Orlo Porter, who accuses him of following Vanessa Cook to Maiden Eggesford and threatens to tear his insides out with his bare hands if he goes near her again.Chapters 6–7, the woods
Bertie delivers Vanessa's message to a jealous, suspicious Orlo in the inn's private bar, and Orlo cheers up only on hearing Bertie will go for a walk during the meeting.Chapter 8, the Goose and Grasshopper
Bertie tells Orlo Porter he will give Vanessa up to him and advises him to tackle Cook for his money after dinner, and the two part bosom pals.Chapter 16, the Goose and Grasshopper
Bertie stumbles into Cook's swimming-pool and enjoys the rinse, then rescues Orlo Porter, who has fallen in fleeing the dog after Cook refused to give him his money.Chapter 17, the swimming-pool
Breakfasting at the Goose and Grasshopper, Bertie learns from Orlo that he and Vanessa were reconciled in the pool last night and are eloping this morning in Cook's Bentley.Chapter 18, the dining-room
Orlo leaves Bertie a letter for Cook announcing the elopement; Bertie decides to post it, but Cook bursts in with Major Plank.Chapters 18–19, Wee Nooke

Every dealing, in order

Chapter 2Orlo Porter was on the same staircase at Oxford as Bertie Wooster (earlier)
Chapter 2Orlo Porter sold an accident policy to Bertie Wooster (earlier)
Chapter 2Bertie Wooster hides from the police Orlo Porter
Chapter 2Orlo Porter orders about Bertie Wooster
Chapter 2Orlo Porter is jealous of Bertie Wooster
Chapter 2Bertie Wooster plays down his past with Vanessa to Orlo Porter
Chapter 2Orlo Porter talks into signing a life policy Bertie Wooster
Chapter 6Orlo Porter asks to stop snoring Bertie Wooster
Chapter 6Orlo Porter accuses of following Vanessa to steal her from him Bertie Wooster
Chapter 6Bertie Wooster denies pursuing Vanessa to Orlo Porter
Chapter 6Orlo Porter spied on through his binoculars Bertie Wooster
Chapter 6Orlo Porter threatens to tear the insides out of Bertie Wooster
Chapter 6Bertie Wooster was at Oxford with Orlo Porter (earlier)
Chapter 7Orlo Porter threatens to tear the insides out of Bertie Wooster
Chapter 7Bertie Wooster fears Orlo Porter
Chapter 7Orlo Porter dislikes Bertie Wooster
Chapter 7Bertie Wooster drove away from the police to safety Orlo Porter (earlier)
Chapter 8Orlo Porter suspects of stealing his girl Bertie Wooster
Chapter 8Orlo Porter loathes Bertie Wooster
Chapter 8Orlo Porter warns never to kiss Vanessa Bertie Wooster
Chapter 8Bertie Wooster carries Vanessa's message to Orlo Porter
Chapter 9Orlo Porter sold accident and life policies to Bertie Wooster (earlier)
Chapter 14Orlo Porter is jealous of Bertie Wooster
Chapter 14Orlo Porter threatened to tear out the insides of Bertie Wooster (earlier)
Chapter 14Orlo Porter threatens by telephone to pull off the head of Bertie Wooster
Chapter 14Bertie Wooster fears Orlo Porter
Chapter 14Bertie Wooster resolves to urge Jeeves's plan on Orlo Porter
Chapter 15Orlo Porter thought the worst of Vanessa's visits to Bertie Wooster (earlier)
Chapter 16Orlo Porter was hostile to and threatened to disembowel Bertie Wooster (earlier)
Chapter 16Bertie Wooster gives up Vanessa in favour of Orlo Porter
Chapter 16Orlo Porter calls a louse, then apologises to Bertie Wooster
Chapter 16Orlo Porter likens to Cyrano de Bergerac Bertie Wooster
Chapter 16Bertie Wooster persuades to tackle Cook again Orlo Porter
Chapter 16Orlo Porter makes friends with Bertie Wooster
Chapter 17Bertie Wooster rescues from drowning Orlo Porter
Chapter 17Orlo Porter gets on first-name terms with Bertie Wooster
Chapter 17Bertie Wooster advised to tackle Cook after dinner Orlo Porter (earlier)
Chapter 17Orlo Porter once wanted to tear out the insides of Bertie Wooster (earlier)
Chapter 17Bertie Wooster reassures about the dog Orlo Porter
Chapter 17Bertie Wooster hides his real errand from Orlo Porter
Chapter 18Orlo Porter tells to take his letter to Bertie Wooster